As for a hydrogen-containing fluoroolefin compound, a hydrogen-containing fluoroolefin compound having 4 to 6 carbon atoms is well known. Patent Literature 1 suggests a method for producing 1H,2H-hexafluorocyclopentene which is an unsaturated hydrogen-containing fluoroolefin compound having 4 to 6 carbon atoms. Specifically, a method is disclosed in which 1,2-dihalogenohexafluorocyclopentene, which serves as a starting material, is reduced by a hydrogen gas in the presence of a catalyst which consists mainly of copper, iron, chromium, or nickel, thereby obtaining 1H,2H-hexafluorocyclopentene as a main product.
On the other hand, as for a method for producing 1,1,2,2,3,3,4-heptafluorocyclopentane which is a saturated hydrogen-containing fluoroolefin compound, methods are suggested in each of which 1-chloroheptafluorocyclopentene, which serves as a starting material, is reduced by hydrogen gas in the presence of a supported catalyst containing at least palladium (see Patent Literatures 2 and 3).
Further, according to Non Patent Literature 1, hexafluorocyclobutene is treated with a metal hydride, thereby obtaining 1H-pentafluorocyclobutene.
According to Non Patent Literature 2, hexafluorocyclobutane, which can be obtained by causing lithium hydride aluminum hydrido to reduce dichlorohexafluorocyclobutane, is subjected to an alkali treatment, thereby obtaining 1H-pentafluorocyclobutene.